Benzoylalkylaminoethanols and process of making same.



. UNITED STATEs EXTENT OFFICE.

'rHAnnAEUs MI EwIoa'or BERLIN, GERMANY, ASSIGNOR TO CHEMISGHE FABRIK AUFACTIEN, voRM. E. sonsamea or BERLIN, GERMANY.

.BENZOYLALKYLAMINOETHANOLS AN-D Paocnzss wanna-ME.

Application filed Septembeilfl, 1905. Serial No; 278,900- (Specimens-lSpecification of Letters Patent.

Patentgd April 10, lacs:

- ethanols,whichpossessanesthetic r erties,

rid and the like.

may be obtaine by treating the a aminoethanols as such or inthe form oftheir salts with benzoylating agents-such as, for example, bBDZOlCitOldanhydrid or benzoylchlo- The composition of the so-formedbenzoylalkylaminoethanols corre sponds to the chemical formula:

. cimcoocarcmn x in which formula R is meant for an alkyl roup, and R,for a hydrogen atom which can e replaced by an alkyl group.

The bases expressed by the before-mentioned formula are insoluble inwater and decompose upon boiling with alkalies into benzoic acid and thecorresponding aminoalcohol. The bases combine with inorganic and organicacids, thus forming the correspond- I ing salts, which possessanesthetic properties.

The hydrochlonc-acid salts of said bases are easily soluble in water.

Ewamp les.

aminoethanol:

2.5 kilograms of diethylaminoethanol (see Ber'ichte cler Deutsche'aUhemischen .Gesell- I schaft, Vol. XIV, pages 1878) are dissolvedin onekilogram of water and while heating 7.5 kilograms of benzoic-acidanhydrid are gradually added to the solution. tion of the reaction themixture is aci ed with dilutehydrochloric acid, the precipi tatedbenzoic acid removed by filtration and by shakin with ether, and thebaseset free by the ad ition of soda. The free base is a schaft, VolXIV,

The

After com lethick oil which has. not up to the present beencrystallized. The hydrochloric-acid salt when crystallized out ofethereal alcohol forms fine long needles melting at 124 to 125centigrade, which are very soluble in water-viz., 1n the ratio of 1:0.4at 15 centigrade It is therefore considerably more easily soluble thanthe hydrochlorates of the known local anesthetics. I

Second. The manufacture of benz0yl-d'imetkylaminoethanol. This compoundis roduced in the manner described in the exam is, but using'dimethlaminoethanol. (See emchtederDeutschenO emischenGesellage 2408, and Vol.XXII, page 114;.) The ree base is also a thick oil. hfydrochloric-acidsalt when crfyl stallized out o 'a mixture of alcohol and et er formssmall white leaves meltin at 136 to 137 centigrade. It is easil solublein water and alcohol, insoluble in ct er.

Third. Benzoyl monomethylaminocthanoZ:

us (1.11,.cooomornng emulsion first roduced the hydrochloric acid' saltof benzoy methylaminoethanol separates out after some time in largeshiny leaves, melting at 108 to 109 centigrade. The base is athick oil.v

Fourth. Benzoyl-d'iisoamylaminoethwnol- 1.02 kilo arms of.diisoamylaminoethanol (see ammo. endcr C'hem'ie, Vol. UOC'XVI, page315) are dissolved in five kilogramsof ether and gradually mixed withseven hundred and fifty aims of benzoylchlorid dissolved in three'lograins of ether. After forty-eight hours the precipitated free baseis sucked off.

rst

lograms of benzo c-acid anhydrid for two The filtrate consists mainly,besides the free base, of its hydrochlorate. The product is obtained bydistilling oil the ether, mixing with soda and absorbing the base withether. In order to purify it, the oxalic-acid salt is prepared.Benn)yl-diisoamylaminoethanol oxalate is easily soluble in hot water,difficultly soluble in cold, and crystallizes in fine needles, meltingat 152 to 153 Centigrade. The free base may be crystallized out ofacetic ether-ligroin and melts at 87 to 88 Centigrade.

The salts of the alkylaminoethanols may In order to producebenzoyl-diisoamylaminoethanol, I may proceed, for example, as follows:Two kilograms of diisoamylaminoetln anol hydrochlorid and 1.4 kilogramsof henzoylchlorid are heated on an oil-bath to about 135 Centigradeuntil the smell of benzoylchlorid has disappeared. The product of thereaction is mixed with water, rendered alkaline with soda, absorbed withether, and transformed, for the purpose of purification, into theoxalate.

I claim as my invention 1. As new chemical products thebenzoylalkylaminoethanols, the constitution of which answers the formulater and decompose upon boiling with alkalies into benzoic acid and thecorresponding amialso butless advanta eou l Y be ben7o latednoalcoholand combinewithin'organic and OIL y game acids to form thecorresponding salts which have anesthetic properties. i

2. The process of producing the herein-described new compounds, whichconsists in reacting on alkylaminoethanols with benzoylating agents andseparating the product of the reaction, substantially as set forth.

In testimony whereof I have hereunto set my hand this 4th day ofSeptember, 1905.

THADDAEUS EMILEWIGZ.

Witnesses HENRY HASPER, WOLDEMAR HAUPT.

